Implementation of design of experiments for optimization of forced degradation conditions and development of a stability-indicating high-performance liquid chromatography method for sepiwhite.

Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101088554 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1615-9314 (Electronic) Linking ISSN: 16159306 NLM ISO Abbreviation: J Sep Sci Subsets: MEDLINE

Original Publication: Weinheim, Germany : Wiley-VCH, c2001-

Chromatography, High Pressure Liquid/*methods ; Dermatologic Agents/*chemistry ; Hyperpigmentation/*prevention & control; Computer Simulation ; Dermatologic Agents/therapeutic use ; Humans ; Limit of Detection ; Reproducibility of Results

Sepiwhite is a novel anti-pigmenting agent that is derived from fatty acid and phenylalanine and used for hyperpigmentation induced by light exposure or inflammation. In this study, a simple and validated high-performance liquid chromatography method for the quantitation of sepiwhite was developed. Optimized forced degradation of sepiwhite at thermal, acid/base, photolysis, oxidative, and heavy metal ions conditions were evaluated and the effect of each of them on production of specific 10%-30% degradants was studied by the approach of design of experiments. Sepiwhite accelerated study was conducted and toxicity of sepiwhite at each condition was tested. An optimized high-performance liquid chromatography method was validated by a face-centered central composition design. Ten different degradants were identified from sepiwhite and degradation behavior under different conditions was studied. Sepiwhite and its degradant products show no cytotoxicity. This optimized high-performance liquid chromatography method can be applied for quality control assay and sepiwhite degradation behavior may be considered in the manufacturing of sepiwhite products.
(© 2021 Wiley-VCH GmbH.)

Bissett DL, Robinson LR, Raleigh PS, Miyamoto K, Hakozaki T, Li J, Kelm GR. Reduction in the appearance of facial hyperpigmentation by topical N-acetyl glucosamine. J Cosmet Dermatol. 2007;6:20-6.
Parvez S, Kang M, Chung HS, Cho C, Hong MC, Shin MK, Bae H. Survey and mechanism of skin depigmenting and lightening agents. Phytother Res. 2006;20:921-34.
Kooyers T, Westerhof W. Toxicology and health risks of hydroquinone in skin lightening formulations. J Eur Acad Dermatol Venereol. 2006;20:777-80.
Nordlund J, Grimes P, Ortonne JP. The safety of hydroquinone. J Eur Acad Dermatol Venereol. 2006;20:781-7.
Colón LE, Johnson LA, Gottschalk RW. Cumulative irritation potential among metronidazole gel 1%, metronidazole gel 0.75%, and azelaic acid gel 15%. Cutis 2007;79:317.
Garcia A, Fulton Jr JE. The combination of glycolic acid and hydroquinone or kojic acid for the treatment of melasma and related conditions. Dermatol Surg. 1996;22:443-7.
Laosirisathian N, Saenjum C, Sirithunyalug J, Eitssayeam S, Sirithunyalug B, Chaiyana W. The chemical composition, antioxidant and anti-tyrosinase activities, and irritation properties of sripanya Punica granatum peel extract. Cosmetics 2020;7:7.
Maddin S. A comparison of topical azelaic acid 20% cream and topical metronidazole 0.75% cream in the treatment of patients with papulopustular rosacea. J Am Acad Dermatol. 1999;40:961-5.
Bourkaib MC, Delaunay S, Framboisier X, Humeau C, Guilbot J, Bize C, Illous E, Chevalot I, Guiavarc'h Y. Enzymatic synthesis of N-10-undecenoyl-phenylalanine catalysed by aminoacylases from Streptomyces ambofaciens. Process Biochem. 2020;99:307-15.
Katoulis A, Alevizou A, Bozi E, Makris M, Zafeiraki A, Mantas N, Kousta F, Mistidou M, Kanelleas A, Stavrianeas N. A randomized, double-blind, vehicle-controlled study of a preparation containing undecylenoyl phenylalanine 2% in the treatment of solar lentigines. Clin Exp Dermatol. 2010;35:473-6.
Briganti S, Camera E, Picardo M. Chemical and instrumental approaches to treat hyperpigmentation. Pigment Cell Res. 2003;16:101-10.
Halder R, Richards G. Topical agents used in the management of hyperpigmentation. Skin ther lett. 2004;9:1-3.
Bolanča T, Cerjan-Stefanović Š, Regelja M, Štanfel D. Ion chromatographic method development for monitoring of seawater quality used in over-the-counter pharmaceutical industry. J Sep Sci. 2005;28:1476-84.
Sangoi MS, Wrasse-Sangoi M, Oliveira PR, Rolim CM, Steppe M. Simultaneous determination of aliskiren and hydrochlorothiazide from their pharmaceutical preparations using a validated stability-indicating MEKC method. J Sep Sci. 2011;34:1859-66.
Helali N, Monser L. Stability indicating method for famotidine in pharmaceuticals using porous graphitic carbon column. J Sep Sci. 2008;31:276-82.
Oliveira de Almeida Leite H, Mohamad Kassab N, Prado MSA, Singh AK. Stability-indicating methods applied in the separation and characterization of the main degradation product of propafenone. J Sep Sci. 2018;1:490-7.
Singh DK, Sahu A, Handa T, Narayanam M, Singh S. Study of the forced degradation behavior of prasugrel hydrochloride by liquid chromatography with mass spectrometry and liquid chromatography with NMR detection and prediction of the toxicity of the characterized degradation products. J Sep Sci. 2015;38:2995-3005.
Abuga KO, Chepkwony HK, Roets E, Hoogmartens J. A stability-indicating HPLC method for the separation of clarithromycin and related substances in bulk samples. J Sep Sci. 2001;24:849-55.
Habib AA, Hammad SF, Amer MM, Kamal AH. Stability indicating RP-HPLC method for determination of dimethyl fumarate in presence of its main degradation products: Application to degradation kinetics. J Sep Sci. 2021;44:726-34.
Ravi TK, Gandhimathi M, Suganthi A, Sarovar S. Forced-degradation study of valdecoxib as bulk drug and in tablet formulation by HPTLC. J Sep Sci. 2006;29:1647-52.
Singh S, Junwal M, Modhe G, Tiwari H, Kurmi M, Parashar N, Sidduri P. Forced degradation studies to assess the stability of drugs and products. Trends Analyt Chem. 2013;49:71-88.
Shah HS, Rubin RF, Lakhwani GR, DiGregorio R, Dave RH. stability of insulin detemir injection in different primary packaging systems at room temperature. J Pharm Pract. 2021;34:253-8.
Shah HS, Sardhara R, Nahar K, Xu T, Delvadia P, Siddiqui A, Gao Z, Selen A, Morris K. Development and validation of sample preparation and an HPLC analytical method for dissolution testing in fed-state simulated gastric fluid-illustrating its application for ibuprofen and ketoconazole immediate release tablets. AAPS PharmSciTech. 2020;21:1-13.
Dar AA, Rath SK, Qaudri A, Singh B, Tasduq SA, Kumar A, Sangwan PL. Isolation, cytotoxic evaluation, and simultaneous quantification of eight bioactive secondary metabolites from Cicer microphyllum by high-performance thin-layer chromatography. J Sep Sci. 2015;38:4021-8.
Yamashita H, Harada M, Misaka J, Takeuchi M, Ikeue K, Anpo M. Degradation of propanol diluted in water under visible light irradiation using metal ion-implanted titanium dioxide photocatalysts. J Photoch Potobio A. 2002;148:257-61.
Arias-Barrau E, Olivera ER, Luengo JM, Fernández C, Galán B, García JL, Díaz E, Miñambres B. The homogentisate pathway: a central catabolic pathway involved in the degradation of L-phenylalanine, L-tyrosine, and 3-hydroxyphenylacetate in Pseudomonas putida. J Bacteriol. 2004;186:5062-77.
Dick L, Dooley N, Elliott MA, Ford SJ, Gordon MR, Halbert GW, Kerr WJ. Boron phenylalanine and related impurities: HPLC analysis, stability profile and degradation pathways. J Pharm Biomed Anal. 2011;56:633-6.
Navarro-Llorens JM, Patrauchan MA, Stewart GR, Davies JE, Eltis LD, Mohn WW. Phenylacetate catabolism in Rhodococcus sp. strain RHA1: a central pathway for degradation of aromatic compounds. J Bacteriol. 2005;187:4497-504.
Parenty AD, Button WG, Ott MA. An expert system to predict the forced degradation of organic molecules. Mol Pharm. 2013;10:2962-74.
Spiteller P, Kern W, Reiner J, Spiteller G. Aldehydic lipid peroxidation products derived from linoleic acid. Biochim Biophys Acta Mol Cell Biol Lipids. 2001;1531:188-208.
Yoshinaga N, Alborn HT, Nakanishi T, Suckling DM, Nishida R, Tumlinson JH, Mori N. Fatty acid-amino acid conjugates diversification in lepidopteran caterpillars. J Chem Ecol. 2010;36:319-25.
Hardt-Stremayr M, Bernaskova M, Hauser S, Kunert O, Guo X, Stephan J, Spreitz J., Lankmayr E., Schmid MG, Wintersteiger R. Development and validation of an HPLC method to determine metabolites of 5-hydroxymethylfurfural (5-HMF). J Sep Sci. 2012;35:2567-74.
Nikolic K, Filijović ND, Maričić B, Agbaba D. Development of a novel RP-HPLC method for the efficient separation of aripiprazole and its nine impurities. J Sep Sci. 2013;36:3165-75.
Samanidou VF, Nika MK, Papadoyannis IN. Development of an HPLC method for the monitoring of tricyclic antidepressants in biofluids. J Sep Sci. 2007;30:2391-400.
Samanidou VF, Pechlivanidou AP, Papadoyannis IN. Development of a validated HPLC method for the determination of four 1, 4-benzodiazepines in human biological fluids. J Sep Sci. 2007;30:679-87.
Sivakumar T, Manavalan R, Muralidharan C, Valliappan K. An improved HPLC method with the aid of a chemometric protocol: simultaneous analysis of amlodipine and atorvastatin in pharmaceutical formulations. J Sep Sci. 2007;30:3143-53.
Peraman R, Bhadraya K, Padmanabha Reddy Y. Analytical quality by design: a tool for regulatory flexibility and robust analytics. Int J Anal Chem. 2015;2015: 868727.
Sausville EA, Peisach J, Horwitz SB. Effect of chelating agents and metal ions on the degradation of DNA by bleomycin. Biochem 1978;17:2740-6.
Kamali H, Atamanesh M, Kaffash E, Mohammadpour F, Khodaverdi E, Hadizadeh F. Elimination of residual solvent from PLGA microspheres containing risperidone using supercritical carbon dioxide. J Drug Deliv Sci Technol. 2020;57:101702.
Song JZ, Qiao CF, Li SL, Han QB, Xu HX. Purity determination of yunaconitine reference standard using HPLC with experimental design and response surface optimization. J Sep Sci. 2008;31:3809-16.
ICHT Guideline. Validation of analytical procedures: text and methodology: Q2(R1). In: International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use; 2005 https://database.ich.org/sites/default/files/Q2%28R1%29%20Guideline.pdf.
Chatzimichalakis PF, Samanidou VF, Verpoorte R, Papadoyannis IN. Development of a validated HPLC method for the determination of B-complex vitamins in pharmaceuticals and biological fluids after solid phase extraction. J Sep Sci. 2004;27:1181-8.
Kurmi M, Kumar S, Singh B, Singh S. Implementation of design of experiments for optimization of forced degradation conditions and development of a stability-indicating method for furosemide. J Pharm Biomed Anal. 2014;96:135-43.
ICHT Guideline. Stability testing of new drug substances and products: Q1A(R2), current step. In: International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use; 2003 https://database.ich.org/sites/default/files/Q1A%28R2%29%20Guideline.pdf.
IBM. IBM RXN for chemistry: the free AI tool in the cloud for digital chemistry. https://rxn.res.ibm.com Last Accessed Mar 10, 2020.
Tseng YC, Tabata Y, Hyon SH, Ikada Y. In vitro toxicity test of 2-cyanoacrylate polymers by cell culture method. J Biomed Mater Res. 1990;24:1355-67.
Wahab MF, Patel DC, Armstrong DW. Total peak shape analysis: detection and quantitation of concurrent fronting, tailing, and their effect on asymmetry measurements. J Chromatogr A. 2017;1509:163-70.
Yang X, Huang M, Zheng S, Ma X, Wan D, Feng Y. Liquid chromatography with mass spectrometry and NMR spectroscopy based discovery of cytotoxic principles from Daphne tangutica Maxim. J Sep Sci. 2016;39:2179-87.

960162 Research Council of Mashhad University of Medical Sciences

Keywords: HPLC method validation; cytotoxicity; degradation products; sepiwhite; stability-indicating method

0 (Dermatologic Agents)

Date Created: 20211020 Date Completed: 20220309 Latest Revision: 20220309

20250114

10.1002/jssc.202100388

34669262